Ethylene carbonate → (R)-4-Benzyl-2-oxazolidinone

HRID 1087753Notes

Reaction equation

HRID 1087753 reaction equation
[NH2:1][C@H:2]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][OH:4].[C:12]1(=O)OCC[O:13]1.C(OCC)(=O)C.O>C1(C)C=CC=CC=1>[CH2:5]([C@@H:2]1[CH2:3][O:4][C:12](=[O:13])[NH:1]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 7303Ethylene carbonateHCID 853475phenylalaninol, (R)-HCID 22728543Water ethylacetate

Product 1

HCID 2734969(R)-4-Benzyl-2-oxazolidinoneYield 78.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3 g of (R)-(+)-2-amino-3-phenylpropanol and 1.8 g of ethylene carbonate in 50 ml toluene in a round bottom flask equipped with a Dean-Stark trap was refluxed for 24 hrs. The reaction mixture was poured into ethyl acetate/water mixture and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with water, followed by brine, dried and concentrated. Kugelrohr distillation at 150°-160° C./0.5 mm Hg provided 2.75 g (75%) of an oil.

Workup

  1. temperaturewas refluxed for 24 hrs
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic extracts were washed with water
  4. customdried
  5. concentrationconcentrated
  6. distillationKugelrohr distillation at 150°-160° C./0.5 mm Hg

Sources & evidence

ORD record
ord-886fa9e778b742ec85ba5d6f0d7f1c7a
Source dataset
uspto-grants-1990_10
Patent number
US04960771

Reaction notes

Loading…